Ask Sean MacPherson how a surfing, skateboarding philosophy major got into the big-time hospitality biz, and he responds as only a surfing, skateboarding philosophy major can: "I was on a spiritual quest – though not too deep of one," he says with a laugh. "After college, my plan was to not have a plan. On the other hand, I always liked building and design, so it felt simultaneously accidental and inevitable."

It would be easy for the guy behind some of New York's hottest hangouts – he owns and designed hotels such as the Bowery, the Jane, and his latest, the Marlton, as well as celebrity-magnet restaurant the Waverly Inn – to be a pretentious jerk. But MacPherson, 49, is disarmingly easygoing and engaged; making people feel welcome, it seems, comes naturally to him – not a bad quality for a hotelier to have. It's an attitude that informs his design philosophy, too. Like his three-floor, 1840s-era West Village townhouse, a former butcher shop he transformed into a spacious home for his family – wife Rachelle and sons Maxwell, two, and Dashiell, four months – MacPherson's hotels and restaurants are layered with references to the past; they feel dramatic but comfortable, lived-in.

As he relaxes into a pleasantly lumpy old couch to discuss his itinerant childhood (raised mostly in Malibu, he hopped the globe with his single mother, herself a champion surfer and avid skier, regularly visiting Mexico, Aspen, and Sun Valley), his days as a Santa Monica skate rat (he ran with the crew featured in the 2001 documentary Dogtown and Z-Boys), and his first gig as a hip-hop promoter (he owned an L.A. nightclub called Funky Reggae), the multitude of influences on his style becomes clear.

"I like everything to have some sort of timelessness to it," he says. "My goal is always to try to create something that could be relevant forever."